Copper(I)-Catalyzed Nitrosylation/Annulation Cascade of Enaminones with tert-Butyl Nitrite: Access to 1H-1,2,3-Triazole 2-Oxides

Abstract

The direct synthesis of triazole 2-oxides has posed a challenge in the field of N-heterocyclic chemistry. A novel copper­(I)-catalyzed nitrosylation/annulation cascade of enaminones provides a straightforward route to 1H-1,2,3-triazole 2-oxides by forming new C–N, N=N, and N–N bonds using noncorrosive tert-butyl nitrite (TBN) as both the N and NO sources. The synthetic protocol features easily accessible starting materials, wide substrate scopes, and good tolerance toward various functional groups while avoiding use of explosive azides.